From Propargylamides to Oxazole Derivatives: NIS-Mediated Cyclization and Further Oxidation by Dioxygen

Hu, Yan‐Cheng; Yi, Ruxia; Wang, Chunxiang; Xin, Xiaoyi; Wu, Fan; Wan, Boshun

doi:10.1021/jo5001719

Cited by 62 publications

(22 citation statements)

References 49 publications

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“…Wan team [55] reported the iodine mediated regioselective annulation of N‐sulfonyl propargyl‐amides 72 through 5‐ exo ‐dig intra‐molecular [56] process that afforded a variety of oxazoles 73 . N,N ‐Dimethylformamide (DMF) was used as an optimal solvent, and a broad substrate scope was illustrated (Scheme 28).…”

Section: Literature Reviewmentioning

confidence: 99%

Recent Progress in Iodine‐Catalysed C−O/C−N Bond Formation of 1,3‐Oxazoles: A Comprehensive Review

et al. 2021

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Over the last few decades, iodine has been a stellar catalyst for numerous organic transformations such as CÀ H activation, hetero-annulation and coupling reactions. In heterocyclic chemistry, iodine is primarily an economical and eco-friendly catalyst that fascinates the construction of CÀ O/CÀ N bonds via oxidative, radical, and electrophilic pathways. Several novel Iodine-catalyzed methodologies have been reported, presenting advances in heterocyclic synthesis with regioselectivity, wide substrate scope and excellent yields. Furthermore, feasible protocols implemented to get oxazole annulation in literature have an enormous impact on new synthetic applications. Therefore, this literature analysis comprises advancements in the field of iodine-mediated 1,3-oxazole synthesis since 1998. For the ease of the readers, the reported methodologies have been categorised based on iodine functioning in reactions with insight into the reaction mechanisms and highlights.

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Section: Literature Reviewmentioning

confidence: 99%

Recent Progress in Iodine‐Catalysed C−O/C−N Bond Formation of 1,3‐Oxazoles: A Comprehensive Review

et al. 2021

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“…58 In 2014, Wan and co-workers reported the iodocyclization of N-propargyl-N-sulfonylamides 100 in the presence of NIS as the halogenating agent to give various 5-acyloxazoles 102 (Scheme 24). 59 When the reaction was performed in N,N-dimethylformamide at room temperature, 5-(1-iodoalkylidene)-4,5-dihydrooxazoles 101 were obtained in good yields. The oxidation of 5-(1-iodoalkylidene)-4,5-dihydrooxazoles 101 into 5-acyloxazoles 102 in the presence of molecular oxygen at 80 °C was further investigated.…”

Section: Scheme 21 Synthesis Of 3-iodoquinolinesmentioning

confidence: 99%

“…quantities and can be carried out in a one-pot fashion. 59 In 2015, they reported a high-yielding formal [3+2] annulation of N-propargyl-N-tosylamides 103a (Z = NTs) to access tetrazoles 104 and dihydroimidazoles 105a (Scheme 24). 60 The cyclization occurs via oxygen-atom transfer from the amide moiety to the alkyne with the intermediacy of NIS as a halogenating source and TMSN 3 as coupling partner.…”

Section: Syn Thesismentioning

confidence: 99%

N-Halo Reagents: Modern Synthetic Approaches for Heterocyclic Synthesis

Andrade¹,

Mattos

2019

Synthesis

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Heterocyclic chemistry is an essential frontier in science and a source of novel biologically active compounds. The development of innovative synthetic methodologies that allows access to different heterocyclic rings is of critical interest to the scientific community. This review will focus on recent applications of N-halo compounds (e.g., N-halosuccinimides, trihaloisocyanuric acids, N-halosulfonamides, etc.) in heterocyclic construction via electrophilic cyclization, asymmetric halocyclization, oxidative cyclization, and radical processes.1 Introduction2 N-Halo Reagent Mediated Heterocyclic Construction and Functionalization2.1 Electrophilic Halocyclizations2.1.1 Asymmetric Halocyclizations2.2 Radical Halocyclizations2.3 Oxidative Halocyclizations2.4 Miscellaneous Halocyclization Reactions3 Summary and Outlook

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“…18 Recently, Hashmi et al reported an elegant synthesis of halogenated oxazoles via the gold-catalyzed formation of alkylideneoxazolines (path e) 19 followed by the halogenation of them (path f). 18 Such a method have been extended to oxazole synthesis with the introduction of heteroatomic or carbon functional groups 20,21 as well as the further oxidation of iodinated alkylideneoxazolines (path g) 22 by Hashmi's and other groups. However, before our report on λ 3 -iodane-mediated oxidative cycloisomerization, 8 these two-step approaches to various functionalized oxazoles has been known.…”

Section: -Iodane-mediated Cycloisomerization/functionalization Reactionsmentioning

confidence: 99%

Metal-free syntheses of oxazoles and their analogues based on λ3-iodane-mediated cycloisomerization/functionalization reactions or [2+2+1] cycloaddition type reactions

Saitô¹

2017

Arkivoc

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As a metal-free construction of oxazoles and furans concomitant with the introduction of oxygen functional groups or fluorine atoms into the side chains, we have developed λ 3 -iodane-mediated cycloisomerization/functionalization reactions of propargyl compounds. In these reactions, aryl-λ 3 -iodane ArI(X)Y works not only as a donor of heteroatomic functional groups but also as an activator of carbon-carbon triple bonds. Therefore, this methodology is not required any transition metal catalysts, which are frequently used in previous methods. Furthermore, this methodology can be extended to λ 3 -iodane-mediated [2+2+1] cycloaddition type reactions of alkynes, nitriles and heteroatoms for metal-free formation of oxazoles and imidazoles.

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From Propargylamides to Oxazole Derivatives: NIS-Mediated Cyclization and Further Oxidation by Dioxygen

Cited by 62 publications

References 49 publications

Recent Progress in Iodine‐Catalysed C−O/C−N Bond Formation of 1,3‐Oxazoles: A Comprehensive Review

Recent Progress in Iodine‐Catalysed C−O/C−N Bond Formation of 1,3‐Oxazoles: A Comprehensive Review

N-Halo Reagents: Modern Synthetic Approaches for Heterocyclic Synthesis

Metal-free syntheses of oxazoles and their analogues based on λ3-iodane-mediated cycloisomerization/functionalization reactions or [2+2+1] cycloaddition type reactions

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